Director of Customer Success & Onboarding

This position is listed on behalf of a partner company, who manages all applications and next steps. Our partner is looking for a Director of Customer Success & Onboarding based in the Canada.

This senior leadership role owns the customer journey across North America, from implementation and onboarding through long-term retention and expansion.
You’ll build and scale a unified Customer Success and Onboarding organization within a rapidly growing SaaS environment.
The position carries direct responsibility for regional net revenue retention and customer experience outcomes.
You’ll establish scalable coverage models, operating processes, playbooks, metrics, and escalation frameworks across a diverse customer portfolio.
You’ll partner closely with commercial, product, support, and technology teams to improve implementations and remove customer friction.
You’ll also help shape AI-powered systems that strengthen onboarding, account health monitoring, and proactive risk management.
With high autonomy and regular customer and team travel, this role is designed for an experienced leader who thrives on ownership, complexity, and measurable impact.

• Own Customer Success and Onboarding strategy across North America, establishing scalable operating models, coverage structures, playbooks, and escalation processes.
• Lead and develop Customer Success and Onboarding teams, including defining organizational structure, roles, responsibilities, and future hiring needs as the region grows.
• Own North American net revenue retention, including renewals, expansions, contraction, customer health, engagement, and revenue performance.
• Manage the end-to-end onboarding and implementation experience, from contract signature through successful go-live, while maintaining high standards for quality, speed, and consistency.
• Define the regional customer experience strategy, operating plan, priorities, headcount requirements, performance metrics, and investments.
• Build strong partnerships with commercial leadership to improve sales-to-onboarding handoffs and ensure customer expectations are aligned from the outset.
• Collaborate with Product and Support teams to identify recurring onboarding challenges, close feedback loops, and improve the overall customer experience.
• Work with channel and technology partners on complex, joint implementations and customer initiatives.
• Serve as the senior customer-facing leader for North America, personally engaging with strategic accounts, escalations, and high-priority implementations when needed.
• Introduce and scale AI-powered capabilities, such as account health scoring and automated risk detection, to improve the efficiency and effectiveness of Customer Success and Onboarding operations.
• Use data and customer insights to identify opportunities, anticipate risks, and continuously improve regional performance.

Requirements

• 7–12+ years of experience in Customer Success, Onboarding, or post-sale leadership within a SaaS environment, with meaningful ownership across both Customer Success and onboarding functions.
• Proven experience building and leading Customer Success and Onboarding organizations of significant scale, including developing managers and senior individual contributors.
• Demonstrated success managing complex, large-scale implementations and rollouts involving numerous internal and external stakeholders.
• Track record of owning revenue-related metrics such as NRR, GRR, renewals, or expansion, with a strong understanding of the operational levers that influence these outcomes.
• Strong senior-level business leadership skills, including the ability to build business cases, advocate for resources, influence decision-making, and operate effectively without relying solely on formal authority.
• Hands-on AI experience equivalent to an advanced level of AI fluency, including responsibility for building or shaping AI-powered tools or systems rather than simply adopting existing solutions.
• Strong strategic, analytical, organizational, and problem-solving capabilities, with the ability to translate customer data and business objectives into scalable operating models.
• Excellent communication and relationship-building skills, with confidence engaging customers, senior executives, and cross-functional leadership.
• High adaptability, resilience, ownership, and comfort operating in a fast-changing, high-performance environment.
• Experience in hospitality technology or hospitality operations is preferred, particularly familiarity with property operations and PMS workflows.
• Experience in a high-growth, international SaaS organization where you have built or evolved operating playbooks is a plus.
• Must reside in one of the eligible U.S. states: Arizona, California, Colorado, Connecticut, Florida, Georgia, Illinois, Kansas, Massachusetts, Montana, Nevada, New Jersey, New York, North Carolina, Ohio, Oregon, South Carolina, Tennessee, Texas, Utah, Vermont, Virginia, Washington, or Wisconsin.
• Willingness to travel regularly across North America for customer visits, team meetings, and company gatherings.

Benefits

• Base salary of $160,500–$181,500 USD .
• Unlimited paid holiday.
• Participation in a company share program.
• Paid parental leave, including up to 6 months fully paid for primary caregivers and 2 months for secondary caregivers after one year of service.
• Annual learning and development budget of €300, with additional support available for high performers.
• Monthly dedicated development time focused on exploring, developing, growing, and elevating skills.
• Work-from-anywhere flexibility, including the ability to work abroad for several weeks each year.
• Relocation options available after one year.
• Home office setup budget and monthly work-from-home allowance.
• Access to AI tools and resources to automate workflows and improve productivity.
• Additional location-specific benefits, which may include healthcare, retirement plans, team events, and other perks.
• Remote-first culture with strong autonomy, professional development, and opportunities to make a significant regional impact.

How Jobgether works:

We use an AI-powered matching process to ensure your application is reviewed quickly, objectively, and fairly against the role's core requirements. Our system identifies the top-fitting candidates, and this shortlist is then shared directly with the hiring company. The final decision and next steps (interviews, assessments) are managed by their internal team.

We appreciate your interest and wish you the best!

Why Apply Through Jobgether?

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